HYDROCARBONS 



'^-l5 



tion with sulfuric acid or gluciu'uiuc acid, or synthesis of a mercapturic 

 acid. 



OCeHgOe 

 ja-Bromophenyl 

 glucuronide 



Br 



Bromo- 

 benzene 



(2) 



OSO^H 

 yo-Bromophenyl sulfuric acid 



Br 



S-CH.CHCOOH S-CHa-CHCOOH 



NH2 



p-Cysteinyl bromo- 

 benzene 



NHCOCH3 



p-Bromophenyl- 

 mercapturic acid 



The Metabolism of Bromobenzene by Oxidation to a Phenol (^) or by Synthesis of 

 Bromomercapturic Acid (^)"" 



The formation of the mercapturic acids was first described in 1879 by 

 Baumann and Preusse^^^ and by Jaffe.^^^ Similar reactions have been 

 noted in the case of all four monohalogen benzenes (fiuorobenzene, chloro- 

 benzene, bromobenzene, iodobenzene), in that each yields a specific mer- 

 capturic acid.'^^'-""' IVIonohalogen naphthalenes and anthracenes also 

 form mercapturic acids. 



0- and w-Dichlorobenzenes (and presumably the other corresponding 

 halogen derivati\'es) like^\'ise give rise to mercapturic acid-^' but p-dichloro- 

 benzene does not.-^^ Likewise, mono- and dichlorotoluenes do not form 

 mercapturic acids. -^^ Callow and Hele^^^ confirmed the fact that 0- 

 chlorotoluene has no influence upon the sulfur metabohsm of the dog. 



238 M. Jaflfe, Ber., 12, 1092-1098 (1879). 



"9 E. Baumann, Z. physiol. Chem., 8, 190-197 (1883). 



2« L. Young and S. H. Zbarsky, J. Biol. Chem., 154, 389-395 (1944). 



"• E. H. CaUow and T. S. Hele, Biochem. J., 20, 598-605 (1926). 



